Isatin based Schiff bases as inhibitors of α-glucosidase: Synthesis, characterization, in vitro evaluation and molecular docking studies

Bioorg Chem. 2015 Jun:60:42-8. doi: 10.1016/j.bioorg.2015.03.005. Epub 2015 Apr 18.

Abstract

Isatin base Schiff bases (1-20) were synthesized, characterized by (1)H NMR and EI/MS and evaluated for α-glucosidase inhibitory potential. Out of these twenty (20) compounds only six analogs showed potent α-glucosidase inhibitory potential with IC50 value ranging in between 2.2±0.25 and 83.5±1.0μM when compared with the standard acarbose (IC50=840±1.73μM). Among the series compound 2 having IC50 value (18.3±0.56μM), 9 (83.5±1.0μM), 11 (3.3±0.25μM), 12 (2.2±0.25μM), 14 (11.8±0.15μM), and 20 (3.0±0.15μM) showed excellent inhibitory potential many fold better than the standard acarbose. The binding interactions of these active analogs were confirmed through molecular docking.

Keywords: Isatin; Molecular docking; Schiff bases; Synthesis; α-Glucosidase inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycoside Hydrolase Inhibitors / chemistry*
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Humans
  • Isatin / analogs & derivatives*
  • Isatin / pharmacology*
  • Molecular Docking Simulation
  • Saccharomyces cerevisiae / enzymology
  • Schiff Bases / chemistry
  • Schiff Bases / pharmacology
  • Structure-Activity Relationship
  • alpha-Glucosidases / metabolism*

Substances

  • Glycoside Hydrolase Inhibitors
  • Schiff Bases
  • Isatin
  • alpha-Glucosidases